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There are 6 clues with the answer 'LOSTABET'
# CLUE
1.
Had to pay up
2.
Order bottle as it is something a risk-taker did (4,1,3)
3.
Had to wear the winning team's jersey, say
4.
Took the wrong side of an over/under, maybe
5.
Had to shave off one eyebrow, say
6.
Had to pay up, maybe